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Chapter 18: Q20. (page 945)

Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.

Short Answer

Expert verified

The mechanism for hydrolysis is shown below.

Step by step solution

01

Formation of Imine

The formation of imine is a reversible process. Most imines can be hydrolysed back into the amines and aldehydes or ketones.The mechanism for the process of hydrolysis of imine is generally the reverse of the mechanism for its formation.

02

Mechanism for the hydrolysis of Benzaldehyde Methyl Imine

The hydrolysis of benzaldehyde methyl imine to benzaldehyde can be shown by the reaction as shown below.

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Most popular questions from this chapter

NMR spectra for two compounds are given here, together with the molecular formulas. Each compound is a ketone or an aldehyde. In each case, show what characteristics of the spectrum imply the presence of a ketone or an aldehyde, and propose a structure for the compound.

Both NaBH4 and NaBD4 are commercially available, and D2O is common and inexpensive. Show how you would synthesize the following labelled compounds, starting with propanone.

(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

(a)

(b)

(c)

Propose a mechanism for each cyanohydrin synthesis just shown.
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